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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.7K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Updated: Sep 21, 2025

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Functional Covalent Layer-by-Layer Thin Films by [2 + 2] Cycloaddition-Retroelectrocyclization.

Hiroyuki Fujita1, Tsuyoshi Michinobu1

  • 1Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

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Summary

Covalent layer-by-layer thin films were created using a novel reaction, forming charge-transfer chromophores for redox activity and silver ion sensing.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Electrochemistry

Background:

  • Layer-by-layer (LbL) thin films offer versatile platforms for advanced material design.
  • Charge-transfer (CT) chromophores are crucial for developing responsive materials.
  • Efficient synthetic routes are needed for fabricating functional thin films.

Purpose of the Study:

  • To fabricate covalent LbL thin films incorporating well-defined CT chromophores.
  • To investigate the redox activities and ion-sensing capabilities of the fabricated films.

Main Methods:

  • Utilized the [2 + 2] cycloaddition-retroelectrocyclization (CA-RE) reaction.
  • Employed dialkylaniline-substituted alkynes and 7,7,8,8-tetracyanoquinodimethane (TCNQ) moieties.
  • Fabricated thin films via a covalent LbL assembly strategy.

Main Results:

  • Successfully synthesized covalent LbL thin films with CT chromophores.
  • Demonstrated potent redox activities in the resulting thin films.
  • Showcased significant Ag+ ion sensing ability attributed to the CT chromophores.

Conclusions:

  • The CA-RE reaction provides an efficient method for creating functional covalent LbL thin films.
  • The fabricated films exhibit promising electrochemical properties and selective ion-sensing capabilities.
  • These materials hold potential for applications in electrochemical sensing and redox-active devices.